#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/07/2200722.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2200722
loop_
_publ_author_name
'Song, Qi'
'Billodeaux, Damon R.'
'Fronczek, Frank R.'
'Fischer, Nikolaus H.'
_publ_section_title
;
 Futoenone, a neolignan from Magnolia soulangiana
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1094
_journal_page_last               o1095
_journal_paper_doi               10.1107/S1600536801017482
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C20 H20 O5'
_chemical_formula_moiety         'C20 H20 O5'
_chemical_formula_sum            'C20 H20 O5'
_chemical_formula_weight         340.36
_chemical_name_common            futoenone
_chemical_name_systematic
;
(2R,4R,5S,5aR)-rel-(-)-4-(1,3-benzodioxol-5-yl)-2,3,4,5-
tetrahydro-7-methoxy-5-methyl-8H-2,5a-methano-benzoepin-8-one
;
_space_group_IT_number           144
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'P 31'
_symmetry_space_group_name_H-M   'P 31'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   7.5210(6)
_cell_length_b                   7.5210(6)
_cell_length_c                   25.2821(13)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    297
_cell_measurement_theta_max      42.6
_cell_measurement_theta_min      23.5
_cell_volume                     1238.50(15)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf-Nonius, 1994)'
_computing_data_reduction        'MAXUS (Mackay et al., 1999)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      297
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  .044
_diffrn_reflns_av_sigmaI/netI    .0309
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4948
_diffrn_reflns_theta_full        74.9
_diffrn_reflns_theta_max         74.9
_diffrn_reflns_theta_min         5.2
_diffrn_standards_decay_%        1.0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .807
_exptl_absorpt_correction_T_max  .724
_exptl_absorpt_correction_T_min  .614
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'trigonal prism'
_exptl_crystal_F_000             540
_exptl_crystal_size_max          .45
_exptl_crystal_size_mid          .34
_exptl_crystal_size_min          .34
_refine_diff_density_max         .23
_refine_diff_density_min         -.17
_refine_ls_extinction_coef       .0076(11)
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         1748
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          .033
_refine_ls_R_factor_gt           .033
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0526P)²+0.0948P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .085
_reflns_number_gt                1727
_reflns_number_total             1748
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ob6082.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Trigonal' changed to 'trigonal' according
to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Trigonal' changed to 'trigonal'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2200722
_cod_database_fobs_code          2200722
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 1.1479(2) .8471(3) .50004(7) .0556(4) Uani d . 1 . . O
O2 1.0624(3) .7416(3) .58724(7) .0585(5) Uani d . 1 . . O
O3 .0405(2) .3643(3) .39544(6) .0447(4) Uani d . 1 . . O
O4 -.0828(3) -.2487(3) .31202(9) .0627(5) Uani d . 1 . . O
O5 .1715(3) -.0237(3) .23485(7) .0586(5) Uani d . 1 . . O
C1 .5913(3) .5173(3) .47896(7) .0339(4) Uani d . 1 . . C
C2 .7965(3) .6495(3) .46484(7) .0360(4) Uani d . 1 . . C
H2 .8337 .6903 .4299 .043 Uiso calc R 1 . . H
C3 .9402(3) .7163(3) .50433(8) .0371(4) Uani d . 1 . . C
C4 .8881(3) .6548(3) .55644(8) .0406(4) Uani d . 1 . . C
C5 .6907(4) .5273(4) .57151(8) .0443(5) Uani d . 1 . . C
H5 .6562 .4872 .6066 .053 Uiso calc R 1 . . H
C6 .5414(3) .4591(3) .53158(8) .0405(4) Uani d . 1 . . C
H6 .4046 .3722 .5405 .049 Uiso calc R 1 . . H
C7 .4204(3) .4515(3) .43851(7) .0332(4) Uani d . 1 . . C
H7 .3009 .3293 .4530 .040 Uiso calc R 1 . . H
C8 .4647(3) .3891(3) .38414(7) .0317(4) Uani d . 1 . . C
H8 .5975 .5008 .3719 .038 Uiso calc R 1 . . H
C9 .4833(4) .1974(4) .38983(9) .0458(5) Uani d . 1 . . C
H9A .5852 .2209 .4160 .069 Uiso calc R 1 . . H
H9B .5231 .1665 .3565 .069 Uiso calc R 1 . . H
H9C .3534 .0840 .4005 .069 Uiso calc R 1 . . H
C10 1.2275(4) .8593(5) .55230(11) .0607(7) Uani d . 1 . . C
H10A 1.3222 .8071 .5522 .073 Uiso calc R 1 . . H
H10B 1.3013 1.0012 .5639 .073 Uiso calc R 1 . . H
C11 .2894(4) .1053(5) .19187(10) .0603(7) Uani d . 1 . . C
H11A .2513 .2079 .1858 .090 Uiso calc R 1 . . H
H11B .2631 .0237 .1605 .090 Uiso calc R 1 . . H
H11C .4328 .1708 .2004 .090 Uiso calc R 1 . . H
C1' .2961(3) .3639(3) .34259(7) .0322(4) Uani d . 1 . . C
C2' .0864(3) .2419(3) .36637(7) .0359(4) Uani d . 1 . . C
C3' -.0398(3) .0420(3) .35842(9) .0444(5) Uani d . 1 . . C
H3' -.1583 -.0298 .3786 .053 Uiso calc R 1 . . H
C4' .0103(3) -.0621(3) .31786(9) .0439(5) Uani d . 1 . . C
C5' .1776(3) .0751(3) .28038(8) .0404(4) Uani d . 1 . . C
C6' .3121(3) .2697(3) .29222(7) .0369(4) Uani d . 1 . . C
H6' .4177 .3481 .2687 .044 Uiso calc R 1 . . H
C7' .3057(3) .5726(3) .33730(8) .0401(4) Uani d . 1 . . C
H7'1 .4457 .6850 .3339 .048 Uiso calc R 1 . . H
H7'2 .2245 .5745 .3078 .048 Uiso calc R 1 . . H
C8' .2118(3) .5766(4) .39009(9) .0425(5) Uani d . 1 . . C
H8' .1629 .6754 .3899 .051 Uiso calc R 1 . . H
C9' .3607(4) .6189(4) .43475(8) .0425(5) Uani d . 1 . . C
H9'1 .2987 .6253 .4678 .051 Uiso calc R 1 . . H
H9'2 .4832 .7511 .4292 .051 Uiso calc R 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O .0492 .0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C3 O1 C10 105.20(19) yes
C4 O2 C10 105.84(19) yes
C2' O3 C8' 107.78(15) yes
C5' O5 C11 115.64(19) ?
C6 C1 C2 119.65(18) ?
C6 C1 C7 119.34(17) ?
C2 C1 C7 120.80(17) ?
C3 C2 C1 117.53(17) ?
C3 C2 H2 121.2 ?
C1 C2 H2 121.2 ?
C2 C3 O1 127.76(19) ?
C2 C3 C4 122.06(18) ?
O1 C3 C4 110.18(18) ?
C5 C4 O2 128.4(2) ?
C5 C4 C3 121.93(18) ?
O2 C4 C3 109.6(2) ?
C4 C5 C6 116.67(18) ?
C4 C5 H5 121.7 ?
C6 C5 H5 121.7 ?
C1 C6 C5 122.16(19) ?
C1 C6 H6 118.9 ?
C5 C6 H6 118.9 ?
C1 C7 C9' 108.71(15) ?
C1 C7 C8 115.04(15) ?
C9' C7 C8 112.98(15) ?
C1 C7 H7 106.5 ?
C9' C7 H7 106.5 ?
C8 C7 H7 106.5 ?
C9 C8 C7 109.86(16) ?
C9 C8 C1' 113.33(15) ?
C7 C8 C1' 110.25(14) ?
C9 C8 H8 107.7 ?
C7 C8 H8 107.7 ?
C1' C8 H8 107.7 ?
C8 C9 H9A 109.5 ?
C8 C9 H9B 109.5 ?
H9A C9 H9B 109.5 ?
C8 C9 H9C 109.5 ?
H9A C9 H9C 109.5 ?
H9B C9 H9C 109.5 ?
O2 C10 O1 109.09(19) ?
O2 C10 H10A 109.9 ?
O1 C10 H10A 109.9 ?
O2 C10 H10B 109.9 ?
O1 C10 H10B 109.9 ?
H10A C10 H10B 108.3 ?
O5 C11 H11A 109.5 ?
O5 C11 H11B 109.5 ?
H11A C11 H11B 109.5 ?
O5 C11 H11C 109.5 ?
H11A C11 H11C 109.5 ?
H11B C11 H11C 109.5 ?
C6' C1' C2' 111.24(15) ?
C6' C1' C7' 115.85(16) ?
C2' C1' C7' 99.03(15) ?
C6' C1' C8 111.95(15) ?
C2' C1' C8 110.03(14) ?
C7' C1' C8 107.97(15) ?
C3' C2' O3 124.81(19) ?
C3' C2' C1' 124.61(19) ?
O3 C2' C1' 110.54(17) ?
C2' C3' C4' 119.05(19) ?
C2' C3' H3' 120.5 ?
C4' C3' H3' 120.5 ?
O4 C4' C3' 123.4(2) ?
O4 C4' C5' 121.0(2) ?
C3' C4' C5' 115.52(18) ?
C6' C5' O5 126.2(2) ?
C6' C5' C4' 121.93(19) ?
O5 C5' C4' 111.84(18) ?
C5' C6' C1' 121.12(18) ?
C5' C6' H6' 119.4 ?
C1' C6' H6' 119.4 ?
C8' C7' C1' 99.15(16) ?
C8' C7' H7'1 111.9 ?
C1' C7' H7'1 111.9 ?
C8' C7' H7'2 111.9 ?
C1' C7' H7'2 111.9 ?
H7'1 C7' H7'2 109.6 ?
O3 C8' C9' 108.35(18) ?
O3 C8' C7' 102.87(17) ?
C9' C8' C7' 111.03(17) ?
O3 C8' H8' 111.4 ?
C9' C8' H8' 111.4 ?
C7' C8' H8' 111.4 ?
C8' C9' C7 111.32(16) ?
C8' C9' H9'1 109.4 ?
C7 C9' H9'1 109.4 ?
C8' C9' H9'2 109.4 ?
C7 C9' H9'2 109.4 ?
H9'1 C9' H9'2 108.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C3 . 1.372(3) ?
O1 C10 . 1.435(3) yes
O2 C4 . 1.377(3) ?
O2 C10 . 1.416(4) yes
O3 C2' . 1.351(3) yes
O3 C8' . 1.473(3) yes
O4 C4' . 1.224(3) yes
O5 C5' . 1.358(3) ?
O5 C11 . 1.431(3) ?
C1 C6 . 1.392(3) ?
C1 C2 . 1.401(3) ?
C1 C7 . 1.519(2) ?
C2 C3 . 1.369(3) ?
C2 H2 . .9300 ?
C3 C4 . 1.386(3) ?
C4 C5 . 1.359(3) ?
C5 C6 . 1.402(3) ?
C5 H5 . .9300 ?
C6 H6 . .9300 ?
C7 C9' . 1.537(3) ?
C7 C8 . 1.542(2) ?
C7 H7 . .9800 ?
C8 C9 . 1.523(3) ?
C8 C1' . 1.583(2) yes
C8 H8 . .9800 ?
C9 H9A . .9600 ?
C9 H9B . .9600 ?
C9 H9C . .9600 ?
C10 H10A . .9700 ?
C10 H10B . .9700 ?
C11 H11A . .9600 ?
C11 H11B . .9600 ?
C11 H11C . .9600 ?
C1' C6' . 1.491(2) ?
C1' C2' . 1.498(2) ?
C1' C7' . 1.541(3) ?
C2' C3' . 1.332(3) ?
C3' C4' . 1.450(3) ?
C3' H3' . .9300 ?
C4' C5' . 1.499(3) ?
C5' C6' . 1.332(3) ?
C6' H6' . .9300 ?
C7' C8' . 1.517(3) ?
C7' H7'1 . .9700 ?
C7' H7'2 . .9700 ?
C8' C9' . 1.508(3) ?
C8' H8' . .9800 ?
C9' H9'1 . .9700 ?
C9' H9'2 . .9700 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 -.1(3) ?
C7 C1 C2 C3 174.48(18) ?
C1 C2 C3 O1 -179.1(2) ?
C1 C2 C3 C4 .9(3) ?
C10 O1 C3 C2 -177.6(2) ?
C10 O1 C3 C4 2.3(2) ?
C10 O2 C4 C5 179.4(2) ?
C10 O2 C4 C3 -.5(2) ?
C2 C3 C4 C5 -1.2(3) ?
O1 C3 C4 C5 178.9(2) ?
C2 C3 C4 O2 178.76(19) ?
O1 C3 C4 O2 -1.2(2) ?
O2 C4 C5 C6 -179.4(2) ?
C3 C4 C5 C6 .5(3) ?
C2 C1 C6 C5 -.5(3) ?
C7 C1 C6 C5 -175.19(19) ?
C4 C5 C6 C1 .3(3) ?
C6 C1 C7 C9' 91.1(2) ?
C2 C1 C7 C9' -83.5(2) ?
C6 C1 C7 C8 -141.08(18) ?
C2 C1 C7 C8 44.3(2) yes
C1 C7 C8 C9 64.9(2) ?
C9' C7 C8 C9 -169.50(17) ?
C1 C7 C8 C1' -169.55(15) ?
C9' C7 C8 C1' -43.9(2) ?
C4 O2 C10 O1 2.0(3) ?
C3 O1 C10 O2 -2.6(3) ?
C9 C8 C1' C6' -46.7(2) ?
C7 C8 C1' C6' -170.28(15) ?
C9 C8 C1' C2' 77.6(2) ?
C7 C8 C1' C2' -46.0(2) ?
C9 C8 C1' C7' -175.35(17) ?
C7 C8 C1' C7' 61.04(19) ?
C8' O3 C2' C3' -174.57(18) ?
C8' O3 C2' C1' 3.3(2) yes
C6' C1' C2' C3' 26.0(3) yes
C7' C1' C2' C3' 148.33(19) ?
C8 C1' C2' C3' -98.7(2) ?
C6' C1' C2' O3 -151.92(16) ?
C7' C1' C2' O3 -29.55(19) yes
C8 C1' C2' O3 83.43(18) ?
O3 C2' C3' C4' 167.15(18) ?
C1' C2' C3' C4' -10.4(3) yes
C2' C3' C4' O4 171.1(2) ?
C2' C3' C4' C5' -12.7(3) yes
C11 O5 C5' C6' -15.0(3) ?
C11 O5 C5' C4' 164.9(2) ?
O4 C4' C5' C6' -163.9(2) ?
C3' C4' C5' C6' 19.8(3) yes
O4 C4' C5' O5 16.2(3) ?
C3' C4' C5' O5 -160.10(18) ?
O5 C5' C6' C1' 176.8(2) ?
C4' C5' C6' C1' -3.1(3) yes
C2' C1' C6' C5' -18.2(3) yes
C7' C1' C6' C5' -130.2(2) ?
C8 C1' C6' C5' 105.4(2) ?
C6' C1' C7' C8' 161.05(16) ?
C2' C1' C7' C8' 42.06(18) yes
C8 C1' C7' C8' -72.52(17) ?
C2' O3 C8' C9' -92.49(18) ?
C2' O3 C8' C7' 25.1(2) yes
C1' C7' C8' O3 -41.81(18) yes
C1' C7' C8' C9' 73.9(2) ?
O3 C8' C9' C7 51.3(2) ?
C7' C8' C9' C7 -60.9(2) ?
C1 C7 C9' C8' 172.37(18) ?
C8 C7 C9' C8' 43.4(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7995055
